Derivatives of amino-naphthol sulphonic acids



Patented Dec. 27, 1932 UNITED STATES PATENT OFFICE enona xamscnnn, or rRAivn'onnoN-TnE ANILINE wonxs, me, on NEW YORK,

-MAIN, GERMAlN'Y, ASSIGNOR 'I'O GENERAL N. Y., .A CORPORATION OF DELAWARE DERIVATIVES OF AMINO-NAPH'IHOL SULPHONIC ACIDS In Drawing. Application filed June 8, 1932, Serial No.

My present invention relates to new derivatives of aminonaphthol sulphonic acids corresponding probably to the general formula wherein R represents a naphthalene radicle, R a phenyl radicle which may contain further substituents, A stands for the group and w means the number 1 or2;

he new compounds are obtained by subjecting the corresponding nitro-aroyl-aminonaphthol sulphonic acids to a reduction process in an alkaline medium by means of for instance glucose, arsenious acid, zinc dust,

sodium sulfide or formaldehyde.

The new compounds do not contain any primary amino-group.

ailinity to the combined with or in substance clear and fast They represent weakly yellowish colored substances and are es are given, the parts 616,157. and in Germany October 4, 1928.

invention is not limited to products norreacting conditions mentioned therein: I

Ewamp-Zel r 38.8 parts of 4'-nitrob'enzoyl-2 amin0-5- naphthol-'F-sulphonic acid are dissolved in 30 parts of a caustic soda solution of 40 B. and about 800 parts of water. The solution is warmed to about C. and then a solution of 16 parts of dextrose in about 100 parts of water is added the temperature being kept for about an hour at 707 5. The yellowish solution thus obtained is neutralized with hydrochlorid acid and the reduction compound is isolated as sodium salt by adding sodium chloride to the aforesaid solution.

, .The'new compound which corresponds to the probable formula SOaH wherein A stands for the group N=N or respectively represents in the form of the free acid yellowish flakes which are insoluble in water. The alkali metal soluble in hot water with a yellow color. The new compound dissolves in concentrated sulphuric acid with an intense brownish orange color. The new compound dyes cotton weakly yellow tints.v Compounds of similar properties are obtained when subjecting 4;'I1itIO-2'-Cl1l010 benzoyl-2-amino-5-naphthol-7-s ul phonic acid or 3-nitro-benzoyl-2-amino- 5 naphthol -7 sulphonic acid to the same reduction process.

Ewample 2 When reducing in the manner as described the particular salts are easily sulphonic acid can in Example 1 4-nitro-benzoyl-2-amino-8- naphthol-6-sulphonic acid the new reduction compound corresponding probably to the formula HO S soln wherein A stands for the group N N respectively is very similar in its properties with the products described in Examplel, but yielding when combined with diazocompounds more bluish dyestuffs.

The 4-nitro-3-chloro-benzoyl 2 amino- 8-naphthol-6-sulphonic acid and the F-nitro- 3' -methoxy-benzoyl-2-amino 8 naphthol 6 be likewise converted into reduction compounds of similar properties.

Ewample 3 f 49 parts of the monosodium salt of the 1 nitro benzoyl 1 amino-8-naphthol-3.6-disulphonic acid are dissolved in 35 parts of a caustic soda lye of 40 B. and about 600 parts of hot water. Then a solution of 16 parts of dextrose in about lOOparts of water is added and the mixture is heated for about an hour at 7 0-7 5. By adding hydrochloric acid the formed reduction product isisolated in the form of reddish yellow flakes. The new compound corresponding probably with the formula wherein A stands for the group respectively is soluble in: water with a yellowish color, in concentrated sulphuric acid with a reddish yellow color. It combines with two molecules of diam-compounds to direct cotton dyestuffs.

The same product is obtained when replacing the 16 parts of dextrose by 15 parts of zinc dust or 12 parts of sodium sulphide and by carrying out the reaction while moderately warming the reaction mass.

I claim: 7 1. Derivatives of amino-naphthol sulphonic acids corresponding probably to the general formula 11 -011 I, HO-RV s'ozn z(sosn wherein Rrepresents a naphthalene radicle, R a phenyl radicle which may contain a further' substituent of the groupconsisting of halogen and alkoxy, A stands forthegroup 1 I N-,N- ,i

and as meansthe number 1 or 2, which products represent weakly yellowish colored substances and are distinguished by an excellent afiinity to the vegetable fiber yielding when combined with diazo-compounds on the fiber or in substance very intense dyestuffs of full, clear and fast shades.

2. Derivatives I of phonic acids corresponding probably to the general formula n-on no-R wherein It represents a naphthalene radicle,

on NH-bOOA -OOO-NH on amino-naphthol sul- A wherein A stands for the group 5 respectively, which product represents in the form of the free acid yellowish flakes which are insoluble in water, forming alkali metal salts which are easily soluble in hot water with a yellow color, which product is soluble in concentrated sulphuric acid with an intense brownish orange color and dyes cotton weakly yellow tints.

4. A derivative of 2-amino-8-naphthol-6- sulphonic acid corresponding pro ably to the formula v s OH OH HOaS wherein A stands for the group no. on! no 01H wherein A stands for the group respectively which product dissolves in water with a yellowish color and in concentrated sulphuric acid with a reddish yellow color and combines with two molecular properties of diazo-compounds to direct cotton dyestufi's.

In testimony whereof, I aflix my signature. GEORG KALISGHER. 

